My mom's house. The beds are comfy, the food is good, and she always gives us a 100% discount off the rack rates. Her pool is just a sprinkler, but I'm not into the pool scene anyway.
That is always a good destination. The food service is very good as well, I find.
In all seriousness, you can't go wrong with St. Augustine - wonderful Spanish colonial architecture, shops, restaurants, a large Spanish fort (and a second smaller one nearby), a lighthouse, beaches, boat trips, etc. Jacksonville is a 45 minute drive to the north and has plenty of its own right (a few nice museums, a great zoo, some very nice historic sites, beaches, outdoor nature areas), and Daytona is only a 30 minute drive south and there is plenty in that area as well.
Tampa/St. Petersburg/Clearwater is a nice destination (we actually honeymooned there). Museums, zoos, aquariums, theme parks, water parks, beaches, shopping...
The keys are lovely, though I would avoid staying on Key West and stay somewhere in the middle around the Marathon vicinity and use Key West as a day trip destination. I can only tolerate Key West proper in small doses.
The southwest coast has many beautiful beaches and barrier islands - not as much to do activity wise as some other areas, but certainly beautiful and relaxing and generally not quite as crowded with tourists.
Panama City and other panhandle area beaches such as Destin and San Destin have nice beaches as well.
Please include favorite resort/hotel, beach, or whatever it is that draws you to that place. Thanks all.
If you can afford more than a few days at a time in places like those you are doing quite well indeed. (More power to ya'.) 
